16 BB-17.] 



ISOPROPYL ALCOHOL 



69 



[BB.] From malonic acid [Vol. II] 

 and ethyl alcohol [14] through ethyl- 

 malonic acid (15 ; T). Or from malonic 

 acid, aldehyde [92], and acetic acid 

 through crotonic acid to nitropropane 

 and n-propylamine (Ibid.}. Or from 

 malonic acid and alcohol [14] and 

 methyl iodide []3] through propanetri- 

 carboxylic and pyrotartarie acids (Ibid.}. 

 Or from malonic and propionic acids 

 through propanetricarboxylie ester, 

 citraconic and pyrotartarie acid (benzyl 

 alcohol [54; M]). 



[CO.] From succinic acid [Vol. II] 

 and ethyl alcohol [14] through ethyl- 

 malonic or pyrotartarie acid (15 ; Y). 



[DD.] From azela'ic acid [Vol. II], 

 propylene being among the products 

 of distillation with soda-lime (Miller 

 and Tschitschkin, Journ. Russ. Soc. 

 31,414; Ann. 307, 375). 



[EE.] From acetoacetic acid (ester) 

 [Vol. II] through pyrotartarie acid or 

 n-propylamine or ethylmalonic acid (15 ; 

 AA ; and benzyl alcohol, 54 ; I). 



[FF.] From malic acid [Vol. II] 

 through pyrotartarie or ethylmalonic 

 acid (15 ; DD). 



[GG-.] From fumaric or male'ic acid 

 [Vol. II] through pyrotartarie or ethyl- 

 malonic acid (15 ; EE). 



[HH.] From tartaric acid [Vol. II] 

 through pyrotartarie acid (15 ; V). 



[II.] From citric acid [Vol. II] 

 through pyrotartarie acid (15 ; W). 



[JJ.] From aconitic acid [Vol. II] 

 through itaconic to pyrotartarie acid 

 (15; X). 



[KK.] From glycocoll [Vol. II] elhyl 

 ester [14] through n-propylamine (15 ; 

 GG) and then as above under C. 



[LL.] From alanine [Vol. II] and 

 methyl alcohol [13] through acrylic to 

 pyrotartarie acid (15 ; HH). 



[MM.] From allyl isothiocyanate 

 [166] through allyl cyanide to crotonic 

 acid (15 ; FF). From crotonic acid 

 through nitropropane and n-propylamine 

 or through pyrotartarie acid (15 ; I). 



[NN.] Choline [Vol. II] gives glycol 

 [45] on boiling the aqueous solution 

 (Wurtz, Ann. Suppl. 6, 200). From glycol 

 and zinc methyl as above under C. 



[OO.] From acetyl carbinol [43] as 

 above under A. 



[PP.] From isobufyric aldehyde [94], 

 which condenses under the influence 

 of alcoholic potash to form 2:2: 4-tri- 

 methylpentane-i : 3-diol (Fossek/Mo- 

 nats. 4, 664 ; Brauchbar, Rid. 17, 641). 

 The latter on oxidation with potassium 

 permanganate gives diisopropyl ketone 

 (Lieben : Franke, Monats. 17, 92 ; 673). 

 From the ketone through the oxime to 

 isopropylamine as above under V. 



17. Normal Butyl Alcohol ; Normal 

 Fropyl Carbinol; 1-Butanol. 



CH 3 .CH 2 .CH 2 .CH 2 .OH 



NATURAL SOURCES. 



A product of fermentation of glycerol 

 in presence of calcium carbonate by 

 Bacillus butylicus and other Schizomy- 

 cetes (Fitz, Ber. 9, 1348; 1O, 276; 

 2226; 11,42; 13, 1311; Vigna, Ber. 

 16, 1438 ; Emmerling, Ber. 29, 2736 ; 

 3O, 451). Butyl alcohol is formed also 

 from mannitol (Fitz, Ber. 10, 280; 11, 

 42; 15, 875; Emmerling, Ber. 3O, 

 452) and from saccharose by this Bacillus 

 (Fitz, Ber. 15, 876), which cannot pro- 

 duce butyl alcohol from dextrose 

 (Emmerling, loc. cit. 453). 



The butyl alcohol producing Bacillus 

 has been found on hay and on rotten 

 wood and is not identical with Granulo- 

 bacter saccharobutyricum of Beyerinck 

 (Centr. Bakter. 15, 171), which can pro- 

 duce butyl alcohol from dextrose and 

 starch, but not from glycerol (Emmer- 

 ling, Ber. 30, 453). 



Granulobacter polymyxa, Beyerinck 

 ( = ? Clostridium polymyxa, Prazmowski), 

 gives a trace of butyl alcohol when 

 grown anaerobically (Lafar's ' Tech- 

 nical Mycology, I/ 189, &c.). 



Micrococcus acidi paralactici and the 

 Bacillus of symptomatic anthrax when 

 grown together in a nutrient solution 

 containing saccharose produce butyl 

 alcohol (Nencki ; Centr. Bakter. 11, 

 225; see also Lafar, 'Techn. My col.' 

 I, 87). 



Bacteria from blue pus can produce 

 butyl alcohol from glycerol during bu- 

 tyric fermentation (Fitz, Ber. 11, 1893). 



The species of butyric ferments com- 



